It was late on a Friday afternoon, and eight of us had gathered in a parking lot to do recon on a route many more cyclists would ride the next evening. I’d been named a marshal for something called the Real Ride, based on my status as an experienced cyclist. I found this ­hilarious. In my mind I took up the sport last week, and on group rides I just follow the person in front of me, who is often otherwise known as the next-to-last in line.

The idea was to check over the lay of the land and note any hazards, because the Real Ride goes through urban areas where broken glass is a major decorating motif. The course was only about 8 miles. Part of the idea was to have people decorate their bikes with lights and glow sticks and enjoy a night ride that is not intimidating unless you tend to get nervous riding in a place where people yell at you to go home and never come back. But there is never very much of that. Mostly, folks clap and cheer in their native languages.

About 1.5 miles in, while we were passing through a city park, five kids on small bikes entered our peloton and started popping wheelies and doing tricky, fishtailing skids, all the more impressive ­because most of their bikes had no brakes and were induced to stop only when one of the riders jammed his Croc-swaddled foot against a bare tire.

Two things occurred to me. One was that I have, for more than a year, dedicated myself exclusively to the task of making a bike go forward with as much speed and consistency as possible. Looking at these kids, all my toil seemed a trifle unimaginative. And two, I was the only person out there on a road bike. The other marshals were serious riders, but like most serious riders they also seem to own some old thing with gears so idiosyncratic only the owner can shift them and a frame that was repainted in a matte color no serious manufacturer would ever consider using. You use that bike for anything under 15 miles. You use it for a different kind of fun—a kind that, I realized, I had been forgetting to have.

The city kids were weaving through our pack of older white people and peppering us with questions about why we were in their ’hood. North of downtown is a concrete structure containing ramps that zig and zag and zig until they let out onto a barbwire-covered walkway leading over an interstate highway. It is impossible to convey the grim Soviet-bloc-public-works-project aspect of the thing. I’d never been inside it, and I was stunned to see our line of bikes turn and enter it. The inside was dark, and the ramps snapped back and forth quickly, forcing us to make sharp turns every three or four pedal strokes. The kids were having a great time, and I was again keenly aware that I was riding a ­spindly greyhound while everyone else was on sturdy Labrador retrievers or, in the case of the kids, medically unsound beagles.

Up on the wire-covered walkway we stopped and Tony, a cycling activist, gave his number to all the kids and told them he’d put brakes on their bikes if they called him. (Last time I checked, they hadn’t.) On the other side of the structure were identical ramps leading down to a rather nice park. We rode out that way and took a different route home. The kids stayed with us the whole way, falling behind only once for a brief, inconclusive fistfight, just to make sure they hadn’t lost track during the evening of who was the alpha male.

“Chaos machines,” said Tony, as they caught up with us and resumed popping wheelies. He meant the kids, not the bikes.

The next morning I drove to the garage where I keep a couple of old bikes. Nobody had touched the good Raleigh for more than a year, and an older ­Raleigh lurked in the shadows, so long neglected that vegetation was beginning to grow on it.

I pumped up the tires and lubed the parts. The older Raleigh afforded me, if anything, a greater, wilder sense of joy. I scraped dead leaves out of the cassette with a Popsicle stick. The gears were unpredictable and jumpy but just workable. I planned to ride the newer one, though, so I decked it out with lights and festive decorations I’d bought at Ocean State Job Lot.

I found something deeply liberating­ about climbing on a crappy, low-­expectations bike. It was all I could do not to blow the whole day painting it a funky matte burnt-orange color. I’m not sure this makes any sense, but I felt like a more authentic cyclist for being around it.

That night 250 people showed up for the ride—a lot more than we had bargained for. I turned out to be a fairly ­terrible marshal, riding next to my friend Liz for 30 minutes until another marshal pulled up and pointed out that the quick-release on her front wheel was unlatched. Liz is a middle-age­ mom, but her bike, in an unintentional tribute to the Chaos Machine kids, had no rear brake. She told me her ex-husband had bought it for her birthday in happier, long-ago days. He drove it home on the roof of his convertible, holding it in place with his left hand. Every old bike has a story.

Nobody got hurt on our ride. And when we came to the hulking Romanian Ceausescu-­regime overpass, I hung back, letting 150 riders or so enter before me. The ramps are encased in screens and bars, so you could see the glow sticks and bike lights swirling upward into the night sky. And like a shabby bike with its cobwebs freshly wiped away, the whole thing became for a moment improbably beautiful.